The night Dina Kaplan met two geeks in a bar on the Bowery, she wasn't looking to switch careers. She was working as a local TV reporter and these guys were ragtag kids. She wouldn't have talked to them, but The Remote Lounge had cameras and telephone handsets at every table to encourage patrons to interact. You could be at Table 4 and think, "I want to see the girls at Table 25." You could send out feelers without really risking rejection.
So when the geeks dared her to venture upstairs, Kaplan took a chance. "Okay," she said. "I'll come up and say hi."
Mike Hudack had dropped out of high school to work for a start-up and his buddy Charles Hope, sporting a nostril pierce and dreadlocks flopping halfway down his chest, was an odd candidate to write software tracking ingredients for a kosher certification company. But it paid the bills. The group talked late into the evening, and Hudack struck Kaplan as some sort of boy genius.
Fast-forward five years and Kaplan was still in touch. By then Hudack and Hope had partnered with two other techies they met at a group called "New York City Geeks," and the guys spent nights and weekends hacking away on an information management program they'd developed, thinking it could form the back-end of a larger company - maybe a platform for TV shows on the Internet.
The hackers now wanted Kaplan to be the face of their operation. She could talk to people, help raise funds or bring in partners, maybe turn their project into a business. Kaplan, who had worked for MTV for four years and been a television reporter for five, could see how Web video might be interesting.
"I trust my instinct on big things," she says. "I remember the date, time, and moment I had my first Starbucks coffee and thinking, 'This company is going to do really well.'"
Kaplan felt the same about Hudack. Though her friends started staging interventions -- did she really want to work with these guys? -- she was ready to gamble. "If I ever know anyone who's going to be the next Bill Gates, it's this guy," she remembers thinking. "If he starts a company, I'll drop whatever I'm doing and go work for him."
Kaplan and her team began to reach out to potential users to see how they might meet their needs. At that point YouTube had launched, but no one had heard of it, and no vernacular existed for the platform they aimed to provide. Written blogs had yet to hit mainstream and "video blogs," as homemade films were then known, were even more fringe. But Hudack responded to requests, and a few months later, they launched at a barbeque in Hoboken, New Jersey. That night they picked up 500 users.
The five first-time entrepreneurs sketched a logo for their company, Blip.tv, on a bar napkin and met in the Winter Garden at the World Financial Center because it had free WiFi. Over the next few months, they attracted more users with better videos, but they had to find a way to make money. Still, none of them had connections. They'd never been part of a start-up community and no one knew angel investors or venture capitalists. Kaplan's immediate task was to raise some cash, so she started going to events every night, asking anyone she met for advice.
That December, Kaplan attended a dinner celebrating women in media at the Paley Center. Joan Gerberding, a radio executive Kaplan knew, asked whom she'd like to meet, and Kaplan said Gerry Laybourne -- a woman to whom she was already indebted.
Years ago, Kaplan had been a politics junkie who ditched college to volunteer for Bill Clinton's presidential campaign. She loved what MTV was doing to encourage young people to get involved in policy and she wanted to be a part.
Laybourne was at the time leading Nickelodeon, the children's network that was part of Viacom, the conglomerate that also owned MTV. After Kaplan learned that Laybourne's husband and son had also attended Wesleyan, Kaplan's alma mater, she wrote Laybourne a passionate letter explaining their connection and requesting an introduction to MTV.
When Laybourne agreed to see her, Kaplan hopped a train from Washington, D.C. to New York for a 15-minute meeting that would jump-start her career. Laybourne contacted the president of MTV News and encouraged him to hire Kaplan, who then worked there from 1995 to 1999.
Ten years later, Kaplan was still grateful. So Joan Gerberding escorted Kaplan to Laybourne's table. "Gerry, this is Dina Kaplan," she said. "She's starting a media company focused on Web video and I think you'll benefit from it."
The next day, Kaplan arrived in Laybourne's office to explain Blip.tv's technology. Laybourne in turn revealed that Oxygen Media, which she'd founded and was running by then, was sponsoring a contest for Mo'Nique's F.A.T. Chance, a reality show featuring plus-sized (that is, "Fabulous And Thick") women in a beauty pageant. Producers wanted to invite women across the country to send in photos and videos celebrating their own curves, and Blip.tv seemed to have the goods to support it.
Oxygen paid Blip.tv a sum in the low five-figures for software enabling consumer-generated content -- in this case, evidence of zaftig hotties in suggestive poses -- to be uploaded on its site, and the contest debuted in April. "Our geeky CTO was looking at large African American women for three months, but that deal changed the future of our company," Kaplan says. "I don't know where we would be today if Gerry hadn't taken that chance on us."
Mo'Nique's F.A.T. Chance online pageant was a hit. It went viral in communities around the nation and established credibility for Blip.tv. Kaplan went back to investors with proof her company could make money. Blip.tv soon raised $550,000 in angel funding and, in subsequent years, $30.3 million from top-tier venture capital firms.
The company, which now goes by "Blip," claims about 330 million video views per month. But eight years ago, when her enterprise was struggling to survive, Kaplan thanked Laybourne, and the media maven's reply stuck with her: "My job right now is to enable the next generation of women leaders."
"This woman probably just changed my life, and I will pay this forward," Kaplan remembers thinking. "With whatever power I have, I want to be the Gerry Laybourne to many future women to come."